Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Cuckold in Chastity

by at_yur_service on Aug 6, 2019
Loving Wives

Mark and Cynthia were out for a walk near their house when they ran across a young, fit asian woman they'd never met before. She introduced herself as Anna, and said that she and her husband Jason lived nearby. Anna proposed that they get together sometime, and they exchanged numbers. Later that week, Anna invited Mark and Cynthia over for dinner and drinks...

Dishpan Hands

by Axelotto on Sep 17, 2017
Loving Wives

There's a special quality about late nights in an airport bar, drinking and shooting the shit with folks you are NEVER going to see again. I heard somebody telling this story while I was drinking away a layover at Dallas-Fort Worth. By the time I thought to turn around and see who was telling the tale, the storyteller was gone. It's probably just a drunkard'...

Clitty Transformation - One Month In

by DivinaTellsAll on Jan 1, 2019
BDSM

Exactly one month ago, on a cold Saturday night in Dallas, Madame Vega and Goddess Kimberly evaluated what I had previously referred to (my entire life), as my cock. This evaluation revealed what I already knew at heart. It was far too tiny and small to be used as a cock, or even considered a cock. I begged them to allow me to embark on a quest that would...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Abducted and Turned Out Ch. 05

by dawnib66 on Sep 19, 2017
Transsexuals & Crossdressers

.... I lapped at her pussy as she intermittently moaned and derided me. "Eat that cunt, you sissy whore. I know you prefer cock, don't you? Answer me slut!" she said as she forced my face deeper into her pussy. "Yes, mistress," I said into her cunt. As I did, she moaned loudly and her pussy spasmed as she gushed into my face. "You are a good little bitch,...

A Cuckold is Seduced Ch. 02

by wants2bsub on Sep 25, 2017
Loving Wives

This is part two of a story involving cuckolding and male power exchange. Please read no further if this offends you. --------- I was on my knees, helping my wife Kelli attach her garter belt to her stockings. I leaned forward and planted on a kiss on her newly trimmed pussy. "Now, now," she said, "Let's save that for Ron." Based on the email that he sen...

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...